Synthesis of 18-substituted steroids Part II (1). Improvements in the preparation of 18-hydroxyprogesterone. |
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| Authors: | D N Kirk M S Rajagopalan |
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| Institution: | Medical Research Council Steroid Reference Collection Chemistry Department, Westfield College, Hampstead, London NW3 7ST. UK |
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| Abstract: | 18-Hydroxyprogesterone is conveniently prepared from 3beta-acetoxypregn-5-en-20beta-ol by a modified route. 3beta-Acetoxy-18-iodopregn-5-en-20-one, obtained by the hypoiodite-photolysis procedure and oxidation, is treated with methanolic silver acetate to give the 18, 20-epoxy-20-methoxy derivative, which crystallises directly without need for chromatography. Hydrolysis of the 3-acetate, and a modified Oppenauer oxidation, gave 18-hydroxy-progesterone in 24% over-all yield. |
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